A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.
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http://dx.doi.org/10.1021/ja310718f | DOI Listing |
J Org Chem
December 2024
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China.
A copper catalyzed enantioselective formal aza-Diels-Alder reaction of formed 1,2-diaza-1,3-dienes from α-halohydrazones and vinyl diazo compounds was described. The protocol provides a variety of optically enriched diazo-containing tetrahydropyridazines in moderate yields and with up to excellent enantioselectivities. The present methodologies utilize chiral oxazolines as the chiral ligands for asymmetric catalysis and feature mild reaction conditions, readily available substrates, and broad substrate scope.
View Article and Find Full Text PDFChem Commun (Camb)
October 2023
Faculty of Chemistry, Institute of Organic Chemistry Lodz University of Technology Żeromskiego 114, 90-543 Lodz, Poland.
In the manuscript the application of dearomative formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines is described. The developed approach utilizes aminocatalytic activation of 2-alkyl-3-furfurals that proceeds formation of the dearomatized dienamine intermediate. Initially obtained cycloadducts have been subjected to subsequent transformations providing access to tetrahydrofuropyridines or functionalized cinnamates.
View Article and Find Full Text PDFOrg Lett
October 2023
Research School of Chemistry, Australian National University, Canberra, Australian Capital Territory 2601, Australia.
J Org Chem
September 2022
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str., 8, Kazan 420088, Russian Federation.
In this article, we report a highly regioselective method for the synthesis of new fused pyridine derivatives─2,3-disubstituted quinolines and 1,2-dihydro-3-pyrazolo[3,4-]pyridin-3-one derivatives. The method is based on the reaction of 1,1-diethoxybutane derivatives with aromatic and heterocyclic nucleophiles. The isolated compounds are similar to the products formed as a result of the Debner-Miller reaction.
View Article and Find Full Text PDFMolecules
October 2020
Aix Marseille Université, CNRS, Centrale Marseille, ISM2, 13397 Marseille, France.
Inversions in the periselectivity of formal aza-Diels-Alder cycloadditions between α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was observed, too. These variations in selectivities were fully rationalized by computational modeling using density functional theory (DFT) methods.
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